Formation of pyridin-4(1H)-one versus 1H-azepin-4(7H)-one by treatment of 4-tert-butyldimethylsilyloxy-2-amino-1-azabicyclo[4.1.0]hept-3-enes with tetrabutylammonium fluoride

被引：12
作者：
Alves, M. Jose [1 ]
Fortes, A. Gil [1 ]
Costa, F. Teixeira [2 ]
Duarte, Vera C. M. [1 ]
机构：
[1] Univ Minho, Dept Quim, P-4710057 Braga, Portugal
[2] Univ Fernando Pessoa, Fac Ciencias Saude, P-4200150 Oporto, Portugal
来源：
TETRAHEDRON | 2007年 / 63卷 / 45期
关键词：
azepinones; pyridinones; aziridines; tetrabutylammonium fluoride;
D O I：
10.1016/j.tet.2007.08.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cycloadducts 3 and 4 were treated with tetrabutylammonium fluoride and rapidly suffer cleavage on the three-membered ring to form either pyridin-4(1H)-one or 1H-azepin-4(7H)-one. When R-1 is an oxycarbonyl or a 2-pyridyl group and R-2 is a negative charge-stabilizing group (cases 3a,b and 4f) the C-C bond cleaves forming products 5. However, when R-2 = H (case 3c) the ring expands to seven members. When R1 is an acyl group the pyridin-4(1H)-one formation includes an unexpected shift of the carbonyl group. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：11167 / 11173
页数：7
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